I thought I'd already reached peak awkward when I ran into one of *those* exes on the express train - nothing, after all, could top 91 blocks of uninterrupted kill-me-now small talk. Then I decided to switch careers. Pride goeth before a fall.
How do you ask strangers and acquaintances to let you bother them for 15-20mins without coming across as a user or pest? Any tips for navigating those meetings so they're not The Worst?
Most people are more than happy to give informational interviews (if not, they're terrible and you don't want to know them anyway). I usually send a friendly email introducing myself, professional goals, and reason for request. I've never had anyone turn me down. When scheduling, always remain very flexible and emphasize that you are available at a time/date most convenient for them.
Yeah, people loooove flattery so just add a line or two of how you were always impressed by their business acumen and how they have inspired you etc. Adoration and some ego-stroking will get you places and they will totally be open to it unless they're a total jerk. Be very flexible and patient because it might literally take them weeks to fit you into their schedule. Remember, the worst they can say is no and if they do they probably don't need to be in your circle anyway.
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